Every year, as the holidays start to take shape, business owners find themselves staring down the same familiar question: what should we do for our people this season?
The sentiment is always there — gratitude, recognition, and a desire to show appreciation. But the best intentions can get buried under end-of-year deadlines, budget crunches, and a rush of last-minute decisions.
This year, I’d encourage leaders to think earlier — and think bigger. Because a holiday gift isn’t just an item or an expense line. It’s an opportunity to make a statement about who you are as a company and how you value the people who make it run.
Give a Gift That Grows
When I was a CEO, I used to look for ways to make a bonus or holiday check stretch beyond the moment. I realized that the best gifts weren’t the flashiest — they were the ones that built something lasting.
That could mean a small ownership stake for key team members, a contribution to an employee’s retirement account, or even helping a young team member open their first investment account.
Those gestures do more than say “thank you.” They say, I believe in your future.
And from my current seat on several boards, I can tell you — the companies that give their employees a path to build wealth tend to keep their talent, strengthen their culture, and attract the kind of people who care about the long game.
Plan Early, Deliver Meaningfully
A meaningful financial gift takes time to plan. If you want to gift shares, profit participation, or structured bonuses, you’ll need your finance and legal teams aligned before the holidays hit.
If you want to contribute to an IRA, a 529, or another long-term account, start those conversations now. The paperwork and setup can take a few weeks — and you’ll want to deliver with clarity, not confusion.
When leaders wait until December to decide, the window for truly meaningful giving closes quickly. Planning early lets you design something intentional — something that reflects your company’s values, not just the calendar date.
Legacy Over Luxury
There’s nothing wrong with a holiday party, a bonus, or a nice gift basket. But the real legacy gift is one that grows — something employees can look back on and say, “That was the year my company helped me take the next step.”
For younger employees, that could mean helping them start an investment habit. For senior staff, it might mean participation in a profit pool or growth fund. For your most trusted team members, perhaps even a path to partial ownership or long-term partnership.
The size of the gift matters less than the intention behind it. When your people see you thinking about their future, they start thinking more seriously about yours.
From the Boardroom Perspective
I’ve watched many leaders learn this lesson the hard way — good people don’t stay for perks, they stay for purpose. And nothing communicates purpose more clearly than investing in someone’s future.
So as the holidays draw near, take a step back and look at your plans. Ask yourself: is this year’s gift something they’ll remember next month, or next decade?
Make it personal. Make it thoughtful. And above all, make it early — because the best gifts take time to wrap right.
This season, let your gratitude grow interest.
Because a good leader gives thanks — but a great one gives opportunity.
